Copper-Catalyzed Regio- and Diastereoselective Additions of Boron-Stabilized Carbanions to Heteroarenium Salts: Synthesis of Azaheterocycles Containing Contiguous Stereocenters

被引：15

作者：

Nallagonda, Rajender ^{[1
]}

Karimov, Rashad R. ^{[1
]}

机构：

[1] Auburn Univ, Dept Chem & Biochem, Auburn, AL 36849 USA

来源：

ACS CATALYSIS | 2021年 / 11卷 / 01期

关键词：

heteroarene dearomatization; diastereoselective synthesis; heterocycles; copper catalysis; dihydropyridines; ENANTIOSELECTIVE ADDITION; NUCLEOPHILIC DEAROMATIZATION; ALLYLIC SUBSTITUTION; GEM-DIBORYLALKANES; DIBORYLMETHANE; ARYLATION; PYRIDINES; REAGENTS; ALKYNES; ROUTE;

D O I：

10.1021/acscatal.0c04474

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

Nucleophilic addition of diborylalkyl reagents to N-alkyl or N-acylpyridinium and related heteroarenium salts has been developed as a key step for the synthesis of nonaromatic nitrogen heterocycles that contain contiguous stereogenic centers. Derivatization of the dihydropyridine products for the synthesis of tetrahydropyridines and piperidines have also been described.

引用

页码：248 / 254

页数：7

共 58 条

[1] Studies toward the synthesis of (+)-palustrine: The first asymmetric synthesis of (-)-methyl palustramate [J].

Angle, SR ;

Henry, RM .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (21) :7490-7497

[2] Nucleophilic Dearomatization of Pyridines under Enamine Catalysis: Regio-, Diastereo-, and Enantioselective Addition of Aldehydes to Activated N-Alkylpyridinium Salts [J].

Bertuzzi, Giulio ;

Sinisi, Alessandro ;

Pecorari, Daniel ;

Caruana, Lorenzo ;

Mazzanti, Andrea ;

Bernardi, Luca ;

Fochi, Mariafrancesca .

ORGANIC LETTERS, 2017, 19 (04) :834-837

[3] Catalytic Enantioselective Addition of Indoles to Activated N-Benzylpyridinium Salts: Nucleophilic Dearomatization of Pyridines with Unusual C-4 Regioselectivity [J].

Bertuzzi, Giulio ;

Sinisi, Alessandro ;

Caruana, Lorenzo ;

Mazzanti, Andrea ;

Fochi, Mariafrancesca ;

Bernardi, Luca .

ACS CATALYSIS, 2016, 6 (10) :6473-6477

[4] Copper-catalyzed coupling of pyridines and quinolines with alkynes: A one-step, asymmetric route to functionalized heterocycles [J].

Black, Daniel A. ;

Beveridge, Ramsay E. ;

Arndtsen, Bruce A. .

JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (05) :1906-1910

[5]

Bonet A, 2014, NAT CHEM, V6, P584, DOI [10.1038/NCHEM.1971, 10.1038/nchem.1971]

[6] Nickel-Catalyzed Enantioselective Arylation of Pyridinium Ions: Harnessing an Iminium Ion Activation Mode [J].

Chau, Stephen T. ;

Lutz, J. Patrick ;

Wu, Kevin ;

Doyle, Abigail G. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (35) :9153-9156

[7] Iridium-catalyzed diborylation of benzylic C-H bonds directed by a hydrosilyl group: synthesis of 1,1-benzyldiboronate esters [J].

Cho, Seung Hwan ;

Hartwig, John F. .

CHEMICAL SCIENCE, 2014, 5 (02) :694-698

[8] Diastereoselective addition of prochiral metallo enolates to chiral 1-acylpyridinium salts [J].

Comins, DL ;

Kuethe, JT ;

Hong, H ;

Lakner, FJ ;

Concolino, TE ;

Rheingold, AL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (11) :2651-2652

[9] Enantiomerically Enriched Tris(boronates): Readily Accessible Conjunctive Reagents for Asymmetric Synthesis [J].

Coombs, John R. ;

Zhang, Liang ;

Morken, James P. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (46) :16140-16143

[10] Copper-catalyzed cross-coupling reactions of epoxides with gem-diborylmethane: access to γ-hydroxyl boronic esters [J].

Ebrahim-Alkhalil, Ahmed ;

Zhang, Zhen-Qi ;

Gong, Tian-Jun ;

Su, Wei ;

Lu, Xiao-Yu ;

Xiao, Bin ;

Fu, Yao .

CHEMICAL COMMUNICATIONS, 2016, 52 (27) :4891-4893

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